Diisopropylethylamine → 5-{2-[4-(4-Ethoxymethyl-5-phenyl-oxazol-3-yl)-piperidin-1-yl]-ethyl}-2-methoxy-benzenesulfonamide

HRID 2288991노트

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HRID 2288991 반응식
[CH2:1]([O:3][CH2:4][C:5]1[N:6]=[C:7](C2CCNCC2)[O:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:2].Cl[CH2:23][CH2:24][C:25]1[CH:26]=[CH:27][C:28]([O:35][CH3:36])=[C:29]([S:31]([NH2:34])(=[O:33])=[O:32])[CH:30]=1.[NH2:37][C@H:38](C(O)=O)[CH2:39][C:40]1C=C2C(C=CC=C2)=[CH:42][CH:41]=1.CCN(C(C)C)C(C)C>O1CCOCC1>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH:40]2[CH2:39][CH2:38][N:37]([CH2:23][CH2:24][C:25]3[CH:26]=[CH:27][C:28]([O:35][CH3:36])=[C:29]([S:31]([NH2:34])(=[O:33])=[O:32])[CH:30]=3)[CH2:42][CH2:41]2)[CH2:7][O:8][C:9]=1[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH3:2]

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 1859152-NaphthylalanineHCID 187004234-(4-Ethoxymethyl-5-phenyl-oxazol-2-yl)-piperidineHCID 187004435-(2-Chloroethyl)-2-methoxy-benzenesulfonamide

생성물 1

HCID 187004565-{2-[4-(4-Ethoxymethyl-5-phenyl-oxazol-3-yl)-piperidin-1-yl]-ethyl}-2-methoxy-benzenesulfonamide

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

To 4-(4-ethoxymethyl-5-phenyl-oxazol-2-yl)-piperidine (0.150 g), prepared as in Intermediate 4, in dioxane is added 5-(2-chloro-ethyl)-2-methoxy-benzenesulfonamide (0.170 g), prepared as in Intermediate 1, Nal (0.012 g) and DIEA (0.274 ml). After heating at 100° C. for 18 hours, the reaction mixture is partitioned between EtOAc and dilute NaHCO3 solution. The organic phase is washed with saturated brine, dried (NaSO4) and concentrated. The residue is dissolved in 1:1 MeOH-CH2Cl2 and preadsorbed onto silica gel. Purification by flash chromatography on silica gel using a MeOH-EtOAc gradient (2-20%), affords the title compound as a white solid.

후처리

  1. customthe reaction mixture is partitioned between EtOAc and dilute NaHCO3 solution
  2. washThe organic phase is washed with saturated brine
  3. dry with materialdried (NaSO4)
  4. concentrationconcentrated
  5. dissolutionThe residue is dissolved in 1:1 MeOH-CH2Cl2
  6. customPurification by flash chromatography on silica gel using a MeOH-EtOAc gradient (2-20%)

출처 및 근거

ORD 기록
ord-2dface9b081c491eaa426a2f50b929d1
출처 데이터셋
uspto-grants-2000_07
특허 번호
US06090825

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